Boron tribromide → HCID 59152646, compound

HRID 250273Notes

Reaction equation

HRID 250273 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([O:15]C)=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([C:6]1[C:10]2[CH:11]=[CH:12][C:13]([OH:15])=[CH:14][C:9]=2[O:8][CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 45489697Ethyl 6-methoxybenzofuran-3-carboxylate

Product 1

HCID 59152646HCID 59152646, compoundYield 68%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

A −78° C. solution of 6-methoxy-benzofuran-3-carboxylic acid ethyl ester (1.50 g, 6.81 mmol) in dichloromethane (20 mL) is treated with boron tribromide (20 mL) dropwise. The mixture is stirred at 0° C. for 60 minutes. The reaction is quenched by adding MeOH (10 mL) dropwise over 10 minutes. The mixture is concentrated. The residue is purified via flash chromatography eluting with 25% EtOAc/hexanes to provide the title compound (0.95 g, 68%). ES/MS m/e 207.0 (M+1), 205.0 (M−1).

Workup

  1. customThe reaction is quenched
  2. additionby adding MeOH (10 mL) dropwise over 10 minutes
  3. concentrationThe mixture is concentrated
  4. customThe residue is purified via flash chromatography
  5. washeluting with 25% EtOAc/hexanes

Sources & evidence

ORD record
ord-8b21c22bbc2d46c2bf3a1ead6bbc9c07
Source dataset
uspto-grants-2011_01
Patent number
US07863302B2

Reaction notes

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